[quote=sandwichsandwich]
@rboab, I think when I first got OWB and the crashes started I wasn't really using mods as I was still playing the full base game before messing with it. By that time I might have had one that increased the 3rd person camera distance and a backpack mod, but nothing particularly fundamental that I would expect could cause such a problem. It's been a while since it started but I think I did try playing with everything disabled and there was no difference. I should check again to be sure; no-one else seems to have had anything like this level of difficulty with it so something's likely gone funny with my setup but I thought it was worth asking, just in case... I think the dialog loop in OWB is quite common though. At the point where you're discussing with your brain whether you want to be reunited your brain talks about the things you've seen and done together; you can get stuck in a repetitive loop talking about the events of Come Fly With Me and That Lucky Old Sun. If you haven't done the quests your brain is referring to it doesn't mention them so the loop doesn't occur. I don't recall the specific dialog tree that gets you there unfortunately; what with all the crashing I don't play OWB very much so my memories are a bit vague.
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That is a vanilla FNV bug. IIRC the wiki also mentions it, let me try and find it.
Here it is, check the first entry in the Bugs section:
http://fallout.wikia.com/wiki/Old_World_Blues_%28quest%29